ent-3α,13-diacetoxy-20-norgibberell-1(10),16-dien-7,19-dioic acid 7methyl ester | 86354-91-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ent-3α,13-diacetoxy-20-norgibberell-1(10),16-dien-7,19-dioic acid 7methyl ester
• CAS: 86354-91-8
• 化学式: C₂₄H₃₀O₈
• 分子量: 446.497
• InChiKey: ILBCJSRRMPBMEF-QYEQFGOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  116.2
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ent-3α,13-diacetoxy-20-norgibberell-1(10),16-dien-7,19-dioic acid 7methyl ester 在 sodium tetrahydroborate 、 草酰氯 、 碘 、 sodium carbonate 、 N,N-二甲基甲酰胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙腈 、 苯 为溶剂， 反应 4.5h， 生成 ent-3α,13-diacetoxy-19,10β-epoxy-1α-iodo-20-norgibberell-16-ene-7-oic acid, 7-methyl ester
  参考文献：
  名称：

  Synthesis, stability and biological activity of 19-desoxy-gibberellins A1 and A3

  摘要：

  The synthetic conversion of gibberellin A3 (GA3) to the 19-desoxy-derivatives of GA1 and GA3 is described. The key steps involve regiospecific reduction of the known GA3 hydrogenolysis product at the C-19 carboxyl group via treatment of the acyl chloride with zinc borohydride, followed by an iodocyclization of the resultant alcohol. 19-Desoxy-GA1 and GA3 are stable in alkali, unlike their parent lactones GA1 and GA3. Both derivatives are biologically active in inducing alpha-amylase production in protoplasts of Avena fatua aleurone. They have biological activities of one order of magnitude less than that of the natural analogues. These data reveal the significant contribution of the lactone carbonyl to the observed response (receptor affinity) of GA1 and GA3.

  DOI：

  10.1016/0031-9422(91)80004-k
• 作为产物：
  描述：

  赤霉素A3甲酯 在 Lindlar's catalyst 吡啶 、 氢气 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 ent-3α,13-diacetoxy-20-norgibberell-1(10),16-dien-7,19-dioic acid 7methyl ester
  参考文献：
  名称：

  Synthesis, stability and biological activity of 19-desoxy-gibberellins A1 and A3

  摘要：

  The synthetic conversion of gibberellin A3 (GA3) to the 19-desoxy-derivatives of GA1 and GA3 is described. The key steps involve regiospecific reduction of the known GA3 hydrogenolysis product at the C-19 carboxyl group via treatment of the acyl chloride with zinc borohydride, followed by an iodocyclization of the resultant alcohol. 19-Desoxy-GA1 and GA3 are stable in alkali, unlike their parent lactones GA1 and GA3. Both derivatives are biologically active in inducing alpha-amylase production in protoplasts of Avena fatua aleurone. They have biological activities of one order of magnitude less than that of the natural analogues. These data reveal the significant contribution of the lactone carbonyl to the observed response (receptor affinity) of GA1 and GA3.

  DOI：

  10.1016/0031-9422(91)80004-k

文献信息

• Synthesis of a 19→10-thiolo analog of the phytohormone gibberellin A1
  作者：G. Adam、A. Schierhorn

  DOI：10.1016/s0040-4039(00)81404-5

  日期：——

  The 19→10-thiololactone analog 7 of the phytohormone gibberellin A1 was synthesized via the Δ1(1)-unsaturated carboxylic acid 2, its transformation to the 19-thiocarboxylic acid 4 and intramolecular photochemical thiolactone ring closure.

  植物激素赤霉素A 1的19→10-硫代内酯类似物7是通过Δ1 （1）-不饱和羧酸2合成的，其转化为19-硫代羧酸4和分子内光化学硫代内酯闭环。
• Schierhorn, Angelika; Adam, Guenter; Kutschabsky, Leo, Journal of the Chemical Society. Perkin transactions I, 1987, p. 2111 - 2118
  作者：Schierhorn, Angelika、Adam, Guenter、Kutschabsky, Leo、Leibnitz, Peter

  DOI：——

  日期：——